198. Sex with Mike, I mean, with Matt

Ok, so those in this picture are way younger than we are, but hey, it’s a nice pic.

I wrote in my last post of Mike’s “request” that I have sex with his friend Matt. I said “yes” without hesitation. For starters, I have already agreed to perform any sexual act on anyone that Mike requests. In addition, I love performing sexually for him, as well as for anyone as I have an exhibitionist side. And it helps that Matt is attractive, and single. As I stated before, the one caveat to my sexploration is that it never involve someone in a relationship unless their partner or spouse is away and condones such activities.

Mike and I had our date night and went out for a nice dinner. As planned we stopped by Matt’s to see his new place and for a night cap. As we pulled up and before I got out of the car, Mike told me to take my panties off, and of course I complied.

We went in and Mike and I were sitting on his couch, with Matt sitting in a nearby chair. We were making small talk, asking him what “single” life felt like after twenty-something years of marriage. I asked Matt if he was dating and he said no, not yet. He said he hadn’t really been trying but only now feels ready to give it a shot. Mike then made some comment like, “So, I guess you haven’t had sex in some time then. That must be something new to get used to, right?”

Matt just laughed and said something like, “Yeah, I guess so.”

Mike then said, “Well, we have something somewhat new in our relationship.” Mike went on to explain to journey into Domestic Discipline and our Dominant/submissive lifestyle. Matt didn’t say much. He was just wide-eyed and said, “Wow, really?” or, “Our you serious?” quiet a bit.

Mike then said, “In fact, I told her to take her panties off in the car just before we came in. Honey, stand up and life up your skirt to show him.”

I immediately stood up and did as Mike told me. Mike said, “So Matt, I guess that’s the first pussy you’ve seen in awhile, isn’t it?”

Matt had this half-laugh and shook his head from side to side and said, “I don’t know what to make of this, but, yeah, it’s been awhile.”

Mike then told me to remove my skirt. Mike stood up and walked over to another chair and sat down. He told me to lay on the couch.

“You know Matt, Jenny likes people to watch her masturbate. Are you interested?” To which he responded, “Um, sure Mike, if that’s okay with you two.”

It has been awhile since I did anything sexual in front of someone for the first time. (Post 20 and Post 139). Mike walked over to me and unbottoned my top and I sat up just enough so he could take it off. He pushed my bra up and exposed by tits and then he sat back down.

I continued to finger myself and play with my tits. I removed my bra after asking Mike for permission to do so. I was looking intently back and forth at Mike and Matt. I love to make eye contact with whomever is watching me. Mike had smile, and Matt’s look was priceless. His eyes were as big as saucers and he had his bottom lipped curled under his top lip and he was slightly moving his head up and down as if to say, “yes, i really like this.”

“Would you like to fuck her?” Mike asked Matt.

“Uh, what? Like, right now? Right here?” Matt stammered.

“Sure,” Mike said nonchalantly, “Right her, right now.”

Matt was hesitant and asked Mike, “Do you have to watch?”

I just kept masturbating as the two of them had a conversation about the logistics of Matt having sex with me. Matt wanted reassurance from Mike that he was cool with it and that I was cool with it. At one point Mike even asked me if I was okay with it to which I replied, “Absolutely.” Matt’s last hangup was having it there with Mike watching, so Mike told him to go ahead and take me to his bedroom if that made him more comfortable. It did, so Mike told me to follow Matt to his room.

I was a little disappointing that Mike wasn’t going to be watching. That’s part of the thrill. Also, I was hoping Mike would join in at some point, but now that didn’t seem likely. Oh well, can’t always have everything you want!

Mike tossed me a condom as I followed Matt to his room. When we got there he closed the door and again asked me if I was okay with this. I told him not only was I okay but he could do me any way he wanted but I wanted to leave the door opened. I said, “At least let Mike hear what’s going on.” Matt complied and opened the door.

I kissed Matt as he and i both started unzipping and removing his pants. I dropped my knees and pulled his underwear down and there it was! Matt has a big penis. I immediately began sucking him and he quickly grew fully erect. I had never had a penis this size in my mouth (I later confirmed with Matt that it was 8.4 inches). I know that isn’t like gargantuan porn-star huge, but still, a personal record for me!

For a moment I wondered if the condom would fit, but it did. And once affixed I got on the bed and laid down on my back and he got on top of me and started fucking me. I was a bit distracted as I was concentrating on the feeling I was getting, trying to determine if his big cock actually felt different. It felt good, very good, but it didn’t really feel different. I kept focusing on what I was feeling hoping to discern some different sensation. I guess after all these years of fucking my vagina is loose enough to accept whatever sized dick without feeling any different. Ha.

I finally gave up trying to identify any different feelings and got back into just enjoying the sex. At some point he flipped me around and entered me doggy style. He then came, but I still had a ways to go. He fingered me for awhile. I asked him if Mike could join us. He said he’d rather “finish me off” on his own. Okay, who am I to complain about that?

He went down on me and I orgasmed about five minutes later. We laid there for awhile, and eventually he said, “Now what?”

I said, “I dunno, I have never done this.” I clarified that I have had sex with other people with Mike’s consent, but I never had it like this, in another room, with Mike waiting. I told him if he was up for another round that I could call Mike in and they both could have me. Matt said maybe later and let’s take this one step at a time. I felt like saying, “Well, what we just did was a mega giant step, so what’s the big deal?” But I kept myself from saying it as that would be rude and I realized Matt was still in a bit of shock over this.

I reassured him this was all very okay and more than just okay, is something I enjoyed tremendously. He got dressed and we walked out of the room together. I was still naked as my clothes were still back in the living room. I surprised Matt when I grabbed his hand and told him I wanted I wanted to hold his hand as we walked back to the living room.

Mike said, “I assume you both enjoyed yourselves?” I replied with a “Yes, Sir,” while Matt sheepishly said, “Yeah, you can say that again.”

Matt sat down and Mike instructed me to kneel next to Matt. Mike asked Matt what he thought about all this and Matt admitted he wasn’t sure what to think as he still isn’t sure what just happened. Mike laughed and said, “Sex with my wife just happened.”

Mike went on to reassure Matt that this was all okay, and that if Matt was okay with it, he could do it again sometime, even that night. Mike told him that I really enjoyed two men at once so if he could join them next time it would be all the more pleasurable to me. Matt said, “I’ve never done that, but sure, we could do that.”

Mike said, “Why not now?” Matt laughingly said, “No, I need more time to recoil. And frankly, I am still in a bit of shock. Let’s just relax a bit and see how it goes.”

Mike agreed and the conversation slowly turned to just mundane talk of what other mutual friends are up to, current events, and stuff like that. At some point Mike again asked Matt if he all three of us should go to his bedroom. Matt said that we should just save that for next time to which Mike responded, “Look, watching Jenny masturbate and hearing you all in the bedroom has me horny, so if you aren’t ready to go again Matt, I sure am. Jen, hon, come suck my dick.”

I got up and went over to where Mike was sitting. I pulled his pants and underwear down, and sucked him where he sat. I kept at it until he came in my mouth. He stood up, pulled up his pants, and said, “Thank you Jen, now get dressed as it is about time to go.”

We stayed about another thirty minutes talking. I wasn’t sure what Matt was making of all of this and whether he was really comfortable with everything that transpired. But he made that clear as we were leaving as he said, “So, are you all free tomorrow night?”

Unfortunately we weren’t, but Mike added, “Matt, you are free to come by our house any evening. Just let me know what works for you. Oh, and by the way, what are you doing Sunday. Want to come to my buddies house and watch football?” Oh my, now there will be Mike, John, and Matt watching the game. Matt is in for one hell of a halftime!

So what do I think of all of this? Well, I share those ruminations on my next post (as well as what happened today during football). Suffice to say, I really enjoy my sex life!!!

Jen that was such an incredible with great description of all the vivid sexy details. I was hanging on every word, wishing I was in the room with you. It is so great that you are able to fulfill on your fantasies and you feel confident enough to ask for and enjoy everything that Mike requires of you. Are there any glass ceilings left to break through. Are there any fantasies left that you would like to do. Of all the things you have done since DD, which are the things that surprise you the most? Also, were all these things fantasies prior to you starting DD?

wow. lots of questions to ponder there. First, I am blushing a bit as I am pleasantly surprised by all the good comments on how I shared the story. I think the whole thing was so playful, joyous, and pleasurable that it came across with how I wrote about it. Okay, as for your questions, I think they are worthy of their own post, so be on the look out for it. Thanks for the idea on what to write about!!